Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones

Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2012, Volume: 77, Number: 18, Pages: 8112-8123 Pages count : 12 DOI: 10.1021/jo301474j

Authors

Shirinian Valerii Z. ¹ , Lonshakov Dmitry V. ¹ , Kachala Vadim V. ¹ , Zavarzin Igor V. ¹ , Shimkin Alexey A. ¹ , Lvov Andrew G. ¹ , Krayushkin Mikhail M. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky prosp., 119991 Moscow, Russian Federation

The bromination of 2,3-diarylcyclopent-2-en-1-ones under various conditions has been studied. It was found that depending on the brominating reagent and nature of solvent the bromine atom can be introduced at the 4- or 5-position of the ethene “bridge”, as well as into the aryl moieties. Aryl group bromination is accomplished with such reagents as molecular bromine, N-bromosuccinimide, or tetrabutylammonium tribromide. 5-Bromocyclopentenones with very high efficiency can be obtained by the reaction with copper(II) bromide in methanol, while 4-bromoketones are prepared in n-propyl acetate. The developed methods can be highly useful for the synthesis of bromo-substituted 2-cyclopenten-1-ones and their close analogues, which are important synthons in organic synthesis and for the preparation of a variety of useful substances.

Shirinian V.Z. , Lonshakov D.V. , Kachala V.V. , Zavarzin I.V. , Shimkin A.A. , Lvov A.G. , Krayushkin M.M.
Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones
Journal of Organic Chemistry. 2012. V.77. N18. P.8112-8123. DOI: 10.1021/jo301474j WOS Scopus OpenAlex

Web of science:	WOS:000308957700033
Scopus:	2-s2.0-84868110959
OpenAlex:	W2128666576

DB	Citing
OpenAlex	35
Scopus	36
Web of science	35